Identifying organic substances

I need to describe experiments to identify unlabelled bottles of the following substances:
butan-2-ol
2-methylpropan-2-ol
butan-1-ol
pent-1-ene
3-iodopropan-1-ol

Okay so I have some ideas, as all of these are either alcohols or alkenes I could start by doing a bromine water test or PCl₅ test to separate the groups. Then for the alcohols I could do tests for primary, secondary and tertiary. But after that I don't know how I would differentiate between butan-1-ol and 3-iodopropan-1-ol, both primary alcohols, and between pent-1-ene and 3-chloroprop-1-ene, both alkenes. I'm guessing it's to do with the halogen atoms, but I don't know how I could do the silver nitrate test as there aren't halide ions in solution, they are covalently bonded. I know that for haloalkanes, adding NaOH solution releases the halide ions into solution, but I don't think that works for haloalcohols or haloalkenes.

Can someone help? Or suggest I completely different method for identifying the substances, maybe I've been going down the wrong path.

tl;dr: I need a test to differentiate haloalcohols from normal alcohols and haloalkenes from normal alkenes.

I think that you are correct with using NaOH to bring the halide ion into solution with subsequent addition of silver ions. It will work with primary haloalkanes and should not be affected by the alcohol group or the alkenyl group.

For differentiation you could always use microscale boiling point (Siwolobov).